# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1zbrcf
_database_code_depnum_ccdc_archive 'CCDC 1827585'
_audit_update_record             
;
2018-03-05 deposited with the CCDC.
2018-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 F9 N3 O6 V'
_chemical_formula_sum            'C24 H21 F9 N3 O6 V'
_chemical_formula_weight         669.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'p 21/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1369(3)
_cell_length_b                   17.7472(9)
_cell_length_c                   20.0446(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.596(3)
_cell_angle_gamma                90.00
_cell_volume                     2854.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2000
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      26.84

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    0.449
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8418
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'IPDS 2T (Stoe & Cie)'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42719
_diffrn_reflns_av_R_equivalents  0.0926
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         26.84
_reflns_number_total             6066
_reflns_number_gt                3787
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0815P)²+0.5064P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6066
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1346
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.74142(7) 0.23089(3) 0.91234(3) 0.04725(16) Uani 1 1 d . . .
F7 F 0.7021(3) 0.18606(16) 1.12978(11) 0.0905(7) Uani 1 1 d . . .
O4 O 0.5780(3) 0.18850(12) 0.84085(11) 0.0528(5) Uani 1 1 d . . .
O2 O 0.8987(3) 0.27880(13) 0.98413(11) 0.0574(5) Uani 1 1 d . . .
F8 F 0.4860(3) 0.12885(16) 1.08392(12) 0.0940(8) Uani 1 1 d . . .
O6 O 0.6290(3) 0.19426(13) 0.98579(11) 0.0560(5) Uani 1 1 d . . .
O1 O 1.0701(3) 0.35621(15) 0.81222(13) 0.0696(7) Uani 1 1 d . . .
O5 O 0.4400(3) 0.41425(13) 0.94639(15) 0.0748(7) Uani 1 1 d . . .
F5 F 0.2485(3) 0.14865(19) 0.81309(17) 0.1153(10) Uani 1 1 d . . .
O3 O 0.8885(4) 0.00438(13) 0.89291(14) 0.0717(7) Uani 1 1 d . . .
N1 N 0.8987(3) 0.27363(14) 0.84631(12) 0.0511(6) Uani 1 1 d . . .
N3 N 0.5905(3) 0.32765(14) 0.90608(13) 0.0523(6) Uani 1 1 d . . .
N2 N 0.8660(3) 0.12585(15) 0.91309(13) 0.0526(6) Uani 1 1 d . . .
F1 F 1.1252(5) 0.43904(17) 1.04645(15) 0.1189(10) Uani 1 1 d . . .
F6 F 0.3092(4) 0.04033(16) 0.78171(19) 0.1219(11) Uani 1 1 d . . .
F9 F 0.4669(4) 0.23545(18) 1.13200(14) 0.1177(11) Uani 1 1 d . . .
F2 F 0.9061(4) 0.3970(2) 1.07722(17) 0.1380(14) Uani 1 1 d . . .
F3 F 1.1249(5) 0.33261(18) 1.09136(14) 0.1201(11) Uani 1 1 d . . .
F4 F 0.3617(4) 0.1367(2) 0.72745(13) 0.1203(11) Uani 1 1 d . . .
C21 C 0.5462(4) 0.38303(18) 0.85630(18) 0.0584(8) Uani 1 1 d . . .
C11 C 0.6229(5) 0.05754(19) 0.85345(18) 0.0623(8) Uani 1 1 d . . .
H11 H 0.5769 0.0097 0.8457 0.075 Uiso 1 1 calc R . .
C10 C 0.5316(4) 0.11853(18) 0.83162(16) 0.0538(7) Uani 1 1 d . . .
C18 C 0.5658(4) 0.2366(2) 1.02740(16) 0.0555(7) Uani 1 1 d . . .
C6 C 0.9242(4) 0.2536(2) 0.78063(16) 0.0557(8) Uani 1 1 d . . .
C4 C 0.9902(4) 0.3337(2) 0.86277(17) 0.0587(8) Uani 1 1 d . . .
C14 C 1.0318(5) 0.1041(2) 0.93570(18) 0.0637(9) Uani 1 1 d . . .
C8 C 0.8496(5) 0.1866(2) 0.74451(17) 0.0698(10) Uani 1 1 d . . .
H8A H 0.7785 0.1618 0.7713 0.105 Uiso 1 1 calc R . .
H8B H 0.9364 0.1527 0.7366 0.105 Uiso 1 1 calc R . .
H8C H 0.7854 0.2015 0.7020 0.105 Uiso 1 1 calc R . .
C3 C 1.0229(5) 0.3722(2) 0.92542(18) 0.0656(9) Uani 1 1 d . . .
H3 H 1.0747 0.4191 0.9281 0.079 Uiso 1 1 calc R . .
C9 C 0.3638(5) 0.1111(2) 0.7889(2) 0.0721(10) Uani 1 1 d . . .
C19 C 0.5153(5) 0.3084(2) 1.01870(18) 0.0644(9) Uani 1 1 d . . .
H19 H 0.4748 0.3329 1.0536 0.077 Uiso 1 1 calc R . .
C5 C 1.0264(5) 0.3040(2) 0.76066(18) 0.0640(9) Uani 1 1 d . . .
C20 C 0.5219(4) 0.34809(18) 0.95761(18) 0.0576(8) Uani 1 1 d . . .
C22 C 0.4557(5) 0.4353(2) 0.8815(2) 0.0722(10) Uani 1 1 d . . .
C12 C 0.7885(5) 0.06534(18) 0.88818(17) 0.0579(8) Uani 1 1 d . . .
C24 C 0.5882(6) 0.3774(2) 0.7866(2) 0.0809(12) Uani 1 1 d . . .
H24A H 0.6558 0.3336 0.7837 0.121 Uiso 1 1 calc R . .
H24B H 0.6484 0.4216 0.7772 0.121 Uiso 1 1 calc R . .
H24C H 0.4873 0.3735 0.7543 0.121 Uiso 1 1 calc R . .
C2 C 0.9792(4) 0.34125(19) 0.98089(17) 0.0582(8) Uani 1 1 d . . .
C13 C 1.0450(5) 0.0304(2) 0.9232(2) 0.0719(10) Uani 1 1 d . . .
C1 C 1.0324(6) 0.3782(2) 1.0489(2) 0.0745(10) Uani 1 1 d . . .
C17 C 0.5529(5) 0.1970(2) 1.09267(18) 0.0686(9) Uani 1 1 d . . .
C15 C 1.1619(5) 0.1572(3) 0.9669(3) 0.0918(14) Uani 1 1 d . . .
H15A H 1.1138 0.2063 0.9696 0.138 Uiso 1 1 calc R . .
H15B H 1.2486 0.1599 0.9398 0.138 Uiso 1 1 calc R . .
H15C H 1.2080 0.1401 1.0115 0.138 Uiso 1 1 calc R . .
C7 C 1.1031(6) 0.3154(3) 0.6988(2) 0.0894(13) Uani 1 1 d . . .
H7A H 1.1741 0.3589 0.7047 0.134 Uiso 1 1 calc R . .
H7B H 1.0168 0.3228 0.6604 0.134 Uiso 1 1 calc R . .
H7C H 1.1676 0.2718 0.6915 0.134 Uiso 1 1 calc R . .
C16 C 1.1830(6) -0.0252(3) 0.9322(3) 0.0986(15) Uani 1 1 d . . .
H16A H 1.1411 -0.0734 0.9157 0.148 Uiso 1 1 calc R . .
H16B H 1.2294 -0.0290 0.9793 0.148 Uiso 1 1 calc R . .
H16C H 1.2678 -0.0090 0.9073 0.148 Uiso 1 1 calc R . .
C23 C 0.3747(7) 0.5068(2) 0.8560(3) 0.1069(18) Uani 1 1 d . . .
H23A H 0.3185 0.5284 0.8899 0.160 Uiso 1 1 calc R . .
H23B H 0.2954 0.4971 0.8158 0.160 Uiso 1 1 calc R . .
H23C H 0.4577 0.5414 0.8457 0.160 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O4 1.937(2) . ?
V1 O2 1.954(2) . ?
V1 O6 1.969(2) . ?
V1 N3 2.103(3) . ?
V1 N2 2.121(3) . ?
V1 N1 2.128(3) . ?
F7 C17 1.329(4) . ?
O4 C10 1.302(4) . ?
O2 C2 1.294(4) . ?
F8 C17 1.327(5) . ?
O6 C18 1.292(4) . ?
O1 C4 1.352(4) . ?
O1 C5 1.390(4) . ?
O5 C20 1.351(4) . ?
O5 C22 1.379(5) . ?
F5 C9 1.308(5) . ?
O3 C12 1.348(4) . ?
O3 C13 1.394(5) . ?
N1 C4 1.311(4) . ?
N1 C6 1.412(4) . ?
N3 C20 1.305(4) . ?
N3 C21 1.404(4) . ?
N2 C12 1.302(4) . ?
N2 C14 1.404(4) . ?
F1 C1 1.322(5) . ?
F6 C9 1.332(5) . ?
F9 C17 1.327(4) . ?
F2 C1 1.298(5) . ?
F3 C1 1.316(5) . ?
F4 C9 1.310(5) . ?
C21 C22 1.335(5) . ?
C21 C24 1.495(5) . ?
C11 C10 1.344(5) . ?
C11 C12 1.416(5) . ?
C11 H11 0.9300 . ?
C10 C9 1.492(5) . ?
C18 C19 1.341(5) . ?
C18 C17 1.504(5) . ?
C6 C5 1.327(5) . ?
C6 C8 1.470(5) . ?
C4 C3 1.415(5) . ?
C14 C13 1.339(5) . ?
C14 C15 1.477(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C3 C2 1.340(5) . ?
C3 H3 0.9300 . ?
C19 C20 1.422(5) . ?
C19 H19 0.9300 . ?
C5 C7 1.492(5) . ?
C22 C23 1.482(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C2 C1 1.511(5) . ?
C13 C16 1.482(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 V1 O2 176.78(10) . . ?
O4 V1 O6 94.46(10) . . ?
O2 V1 O6 85.52(10) . . ?
O4 V1 N3 87.19(10) . . ?
O2 V1 N3 89.59(10) . . ?
O6 V1 N3 88.56(10) . . ?
O4 V1 N2 86.13(10) . . ?
O2 V1 N2 97.10(10) . . ?
O6 V1 N2 89.18(10) . . ?
N3 V1 N2 172.75(11) . . ?
O4 V1 N1 95.05(10) . . ?
O2 V1 N1 85.12(10) . . ?
O6 V1 N1 170.15(10) . . ?
N3 V1 N1 94.44(10) . . ?
N2 V1 N1 88.94(10) . . ?
C10 O4 V1 128.5(2) . . ?
C2 O2 V1 127.6(2) . . ?
C18 O6 V1 125.1(2) . . ?
C4 O1 C5 105.4(3) . . ?
C20 O5 C22 105.7(3) . . ?
C12 O3 C13 105.2(3) . . ?
C4 N1 C6 105.9(3) . . ?
C4 N1 V1 120.6(2) . . ?
C6 N1 V1 133.4(2) . . ?
C20 N3 C21 106.0(3) . . ?
C20 N3 V1 120.2(2) . . ?
C21 N3 V1 133.8(2) . . ?
C12 N2 C14 106.0(3) . . ?
C12 N2 V1 121.4(2) . . ?
C14 N2 V1 132.6(2) . . ?
C22 C21 N3 108.0(3) . . ?
C22 C21 C24 128.8(3) . . ?
N3 C21 C24 123.1(3) . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
O4 C10 C11 126.2(3) . . ?
O4 C10 C9 112.5(3) . . ?
C11 C10 C9 121.3(3) . . ?
O6 C18 C19 127.9(3) . . ?
O6 C18 C17 112.5(3) . . ?
C19 C18 C17 119.5(3) . . ?
C5 C6 N1 108.0(3) . . ?
C5 C6 C8 128.6(3) . . ?
N1 C6 C8 123.4(3) . . ?
N1 C4 O1 112.0(3) . . ?
N1 C4 C3 129.1(3) . . ?
O1 C4 C3 118.7(3) . . ?
C13 C14 N2 108.1(4) . . ?
C13 C14 C15 129.0(4) . . ?
N2 C14 C15 122.9(3) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
F5 C9 F4 105.9(4) . . ?
F5 C9 F6 105.9(4) . . ?
F4 C9 F6 105.9(4) . . ?
F5 C9 C10 112.7(3) . . ?
F4 C9 C10 112.1(3) . . ?
F6 C9 C10 113.7(3) . . ?
C18 C19 C20 121.9(3) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C6 C5 O1 108.7(3) . . ?
C6 C5 C7 135.4(4) . . ?
O1 C5 C7 115.9(3) . . ?
N3 C20 O5 112.0(3) . . ?
N3 C20 C19 128.8(3) . . ?
O5 C20 C19 119.1(3) . . ?
C21 C22 O5 108.2(3) . . ?
C21 C22 C23 134.9(4) . . ?
O5 C22 C23 116.8(4) . . ?
N2 C12 O3 112.7(3) . . ?
N2 C12 C11 129.0(3) . . ?
O3 C12 C11 118.0(3) . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C2 C3 126.8(3) . . ?
O2 C2 C1 113.5(3) . . ?
C3 C2 C1 119.7(3) . . ?
C14 C13 O3 108.0(3) . . ?
C14 C13 C16 135.2(5) . . ?
O3 C13 C16 116.8(4) . . ?
F2 C1 F3 106.6(4) . . ?
F2 C1 F1 107.8(4) . . ?
F3 C1 F1 105.0(4) . . ?
F2 C1 C2 112.2(4) . . ?
F3 C1 C2 111.3(3) . . ?
F1 C1 C2 113.6(3) . . ?
F9 C17 F8 107.6(3) . . ?
F9 C17 F7 105.4(3) . . ?
F8 C17 F7 104.9(3) . . ?
F9 C17 C18 113.4(3) . . ?
F8 C17 C18 113.4(3) . . ?
F7 C17 C18 111.4(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 V1 O4 C10 -147.2(16) . . . . ?
O6 V1 O4 C10 -57.7(3) . . . . ?
N3 V1 O4 C10 -146.0(3) . . . . ?
N2 V1 O4 C10 31.2(3) . . . . ?
N1 V1 O4 C10 119.8(3) . . . . ?
O4 V1 O2 C2 -58.3(18) . . . . ?
O6 V1 O2 C2 -148.0(3) . . . . ?
N3 V1 O2 C2 -59.4(3) . . . . ?
N2 V1 O2 C2 123.4(3) . . . . ?
N1 V1 O2 C2 35.1(3) . . . . ?
O4 V1 O6 C18 -116.3(3) . . . . ?
O2 V1 O6 C18 60.5(3) . . . . ?
N3 V1 O6 C18 -29.2(3) . . . . ?
N2 V1 O6 C18 157.7(3) . . . . ?
N1 V1 O6 C18 78.7(6) . . . . ?
O4 V1 N1 C4 150.8(3) . . . . ?
O2 V1 N1 C4 -26.0(3) . . . . ?
O6 V1 N1 C4 -44.2(7) . . . . ?
N3 V1 N1 C4 63.2(3) . . . . ?
N2 V1 N1 C4 -123.2(3) . . . . ?
O4 V1 N1 C6 -24.5(3) . . . . ?
O2 V1 N1 C6 158.7(3) . . . . ?
O6 V1 N1 C6 140.5(5) . . . . ?
N3 V1 N1 C6 -112.1(3) . . . . ?
N2 V1 N1 C6 61.5(3) . . . . ?
O4 V1 N3 C20 116.6(3) . . . . ?
O2 V1 N3 C20 -63.5(3) . . . . ?
O6 V1 N3 C20 22.1(3) . . . . ?
N2 V1 N3 C20 93.9(8) . . . . ?
N1 V1 N3 C20 -148.5(3) . . . . ?
O4 V1 N3 C21 -66.9(3) . . . . ?
O2 V1 N3 C21 113.1(3) . . . . ?
O6 V1 N3 C21 -161.4(3) . . . . ?
N2 V1 N3 C21 -89.6(8) . . . . ?
N1 V1 N3 C21 28.0(3) . . . . ?
O4 V1 N2 C12 -20.4(3) . . . . ?
O2 V1 N2 C12 159.5(2) . . . . ?
O6 V1 N2 C12 74.1(3) . . . . ?
N3 V1 N2 C12 2.3(9) . . . . ?
N1 V1 N2 C12 -115.6(3) . . . . ?
O4 V1 N2 C14 158.2(3) . . . . ?
O2 V1 N2 C14 -21.9(3) . . . . ?
O6 V1 N2 C14 -107.3(3) . . . . ?
N3 V1 N2 C14 -179(100) . . . . ?
N1 V1 N2 C14 63.0(3) . . . . ?
C20 N3 C21 C22 1.5(4) . . . . ?
V1 N3 C21 C22 -175.4(3) . . . . ?
C20 N3 C21 C24 -174.7(4) . . . . ?
V1 N3 C21 C24 8.4(5) . . . . ?
V1 O4 C10 C11 -25.7(5) . . . . ?
V1 O4 C10 C9 158.1(2) . . . . ?
C12 C11 C10 O4 -2.3(5) . . . . ?
C12 C11 C10 C9 173.6(3) . . . . ?
V1 O6 C18 C19 22.8(5) . . . . ?
V1 O6 C18 C17 -156.5(2) . . . . ?
C4 N1 C6 C5 -1.6(4) . . . . ?
V1 N1 C6 C5 174.2(2) . . . . ?
C4 N1 C6 C8 177.0(3) . . . . ?
V1 N1 C6 C8 -7.2(5) . . . . ?
C6 N1 C4 O1 1.9(4) . . . . ?
V1 N1 C4 O1 -174.5(2) . . . . ?
C6 N1 C4 C3 -173.2(4) . . . . ?
V1 N1 C4 C3 10.4(5) . . . . ?
C5 O1 C4 N1 -1.5(4) . . . . ?
C5 O1 C4 C3 174.2(3) . . . . ?
C12 N2 C14 C13 -0.2(4) . . . . ?
V1 N2 C14 C13 -179.0(2) . . . . ?
C12 N2 C14 C15 179.3(4) . . . . ?
V1 N2 C14 C15 0.5(5) . . . . ?
N1 C4 C3 C2 10.9(6) . . . . ?
O1 C4 C3 C2 -163.9(3) . . . . ?
O4 C10 C9 F5 -56.0(5) . . . . ?
C11 C10 C9 F5 127.6(4) . . . . ?
O4 C10 C9 F4 63.4(4) . . . . ?
C11 C10 C9 F4 -113.1(4) . . . . ?
O4 C10 C9 F6 -176.5(3) . . . . ?
C11 C10 C9 F6 7.1(5) . . . . ?
O6 C18 C19 C20 1.9(6) . . . . ?
C17 C18 C19 C20 -178.9(3) . . . . ?
N1 C6 C5 O1 0.7(4) . . . . ?
C8 C6 C5 O1 -177.8(3) . . . . ?
N1 C6 C5 C7 179.3(4) . . . . ?
C8 C6 C5 C7 0.8(7) . . . . ?
C4 O1 C5 C6 0.4(4) . . . . ?
C4 O1 C5 C7 -178.5(3) . . . . ?
C21 N3 C20 O5 -2.0(4) . . . . ?
V1 N3 C20 O5 175.4(2) . . . . ?
C21 N3 C20 C19 173.7(4) . . . . ?
V1 N3 C20 C19 -8.9(5) . . . . ?
C22 O5 C20 N3 1.8(4) . . . . ?
C22 O5 C20 C19 -174.4(3) . . . . ?
C18 C19 C20 N3 -8.5(6) . . . . ?
C18 C19 C20 O5 167.0(3) . . . . ?
N3 C21 C22 O5 -0.4(4) . . . . ?
C24 C21 C22 O5 175.5(4) . . . . ?
N3 C21 C22 C23 179.1(5) . . . . ?
C24 C21 C22 C23 -5.0(8) . . . . ?
C20 O5 C22 C21 -0.8(4) . . . . ?
C20 O5 C22 C23 179.6(4) . . . . ?
C14 N2 C12 O3 0.7(4) . . . . ?
V1 N2 C12 O3 179.6(2) . . . . ?
C14 N2 C12 C11 -173.9(4) . . . . ?
V1 N2 C12 C11 5.1(5) . . . . ?
C13 O3 C12 N2 -0.8(4) . . . . ?
C13 O3 C12 C11 174.4(3) . . . . ?
C10 C11 C12 N2 11.8(6) . . . . ?
C10 C11 C12 O3 -162.5(3) . . . . ?
V1 O2 C2 C3 -26.8(5) . . . . ?
V1 O2 C2 C1 156.3(3) . . . . ?
C4 C3 C2 O2 -4.0(6) . . . . ?
C4 C3 C2 C1 172.8(4) . . . . ?
N2 C14 C13 O3 -0.3(4) . . . . ?
C15 C14 C13 O3 -179.8(4) . . . . ?
N2 C14 C13 C16 177.5(4) . . . . ?
C15 C14 C13 C16 -2.0(8) . . . . ?
C12 O3 C13 C14 0.6(4) . . . . ?
C12 O3 C13 C16 -177.6(3) . . . . ?
O2 C2 C1 F2 -62.2(5) . . . . ?
C3 C2 C1 F2 120.6(5) . . . . ?
O2 C2 C1 F3 57.1(5) . . . . ?
C3 C2 C1 F3 -120.1(4) . . . . ?
O2 C2 C1 F1 175.3(3) . . . . ?
C3 C2 C1 F1 -1.9(6) . . . . ?
O6 C18 C17 F9 -170.9(3) . . . . ?
C19 C18 C17 F9 9.8(5) . . . . ?
O6 C18 C17 F8 -47.8(4) . . . . ?
C19 C18 C17 F8 132.9(4) . . . . ?
O6 C18 C17 F7 70.3(4) . . . . ?
C19 C18 C17 F7 -109.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.84
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.053
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc1zbrfh
_database_code_depnum_ccdc_archive 'CCDC 1827587'
_audit_update_record             
;
2018-03-05 deposited with the CCDC.
2018-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            V(PyTFP)3
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H15 F9 N3 O3 V'
_chemical_formula_sum            'C24 H15 F9 N3 O3 V'
_chemical_formula_weight         615.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3944(11)
_cell_length_b                   10.6399(13)
_cell_length_c                   13.4756(15)
_cell_angle_alpha                87.461(9)
_cell_angle_beta                 73.130(9)
_cell_angle_gamma                82.194(9)
_cell_volume                     1277.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2000
_cell_measurement_theta_min      1.932
_cell_measurement_theta_max      26.848

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.486
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7645
_exptl_absorpt_correction_T_max  0.9656
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'IPDS 2T (Stoe & Cie)'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11718
_diffrn_reflns_av_unetI/netI     0.0997
_diffrn_reflns_av_R_equivalents  0.1231
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.932
_diffrn_reflns_theta_max         26.848
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             5268
_reflns_number_gt                3233
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5268
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_ref         0.3039
_refine_ls_wR_factor_gt          0.2285
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V001 V 0.49161(7) 0.28690(6) 0.26676(5) 0.0498(3) Uani 1 1 d . . . . .
O1 O 0.3301(3) 0.4243(3) 0.3057(2) 0.0567(7) Uani 1 1 d . . . . .
O2 O 0.6546(3) 0.3872(3) 0.2482(2) 0.0592(8) Uani 1 1 d . . . . .
F1 F 0.2266(4) 0.6797(3) 0.3179(3) 0.0952(11) Uani 1 1 d . . . . .
O3 O 0.6354(3) 0.1352(3) 0.2273(3) 0.0617(8) Uani 1 1 d . . . . .
N3 N 0.3283(4) 0.1543(3) 0.2831(3) 0.0539(8) Uani 1 1 d . . . . .
F3 F 0.1127(6) 0.6602(4) 0.4762(3) 0.1173(16) Uani 1 1 d . . . . .
N2 N 0.5006(4) 0.3219(3) 0.1082(3) 0.0499(8) Uani 1 1 d . . . . .
F2 F 0.0508(4) 0.5646(5) 0.3641(5) 0.1241(16) Uani 1 1 d . . . . .
C16 C 0.3770(5) 0.3179(4) 0.0783(3) 0.0553(9) Uani 1 1 d . . . . .
H16 H 0.2888 0.3043 0.1286 0.066 Uiso 1 1 calc R U . . .
C1 C 0.1669(6) 0.5961(5) 0.3900(4) 0.0713(13) Uani 1 1 d . . . . .
C19 C 0.4997(6) 0.0131(5) 0.1538(4) 0.0643(11) Uani 1 1 d . . . . .
H19 H 0.5078 -0.0418 0.1000 0.077 Uiso 1 1 calc R U . . .
N1 N 0.4860(4) 0.2619(4) 0.4268(3) 0.0583(9) Uani 1 1 d . . . . .
F7 F 0.7749(6) -0.0842(6) 0.0259(5) 0.151(2) Uani 1 1 d . . . . .
C12 C 0.6289(5) 0.3437(4) 0.0360(3) 0.0524(9) Uani 1 1 d . . . . .
C5 C 0.4131(8) 0.3203(7) 0.6050(4) 0.0855(17) Uani 1 1 d . . . . .
H5 H 0.3598 0.3778 0.6569 0.103 Uiso 1 1 calc R U . . .
C20 C 0.3531(5) 0.0528(4) 0.2219(3) 0.0575(10) Uani 1 1 d . . . . .
C13 C 0.6329(6) 0.3571(5) -0.0680(3) 0.0627(11) Uani 1 1 d . . . . .
H13 H 0.7224 0.3691 -0.1175 0.075 Uiso 1 1 calc R U . . .
F5 F 1.0217(4) 0.4038(7) 0.0985(4) 0.144(2) Uani 1 1 d . . . . .
F4 F 0.8910(6) 0.5424(5) 0.1982(6) 0.144(2) Uani 1 1 d . . . . .
C2 C 0.2782(5) 0.4832(4) 0.3951(4) 0.0568(10) Uani 1 1 d . . . . .
C4 C 0.4061(6) 0.3414(5) 0.5043(3) 0.0640(12) Uani 1 1 d . . . . .
C15 C 0.3744(6) 0.3329(5) -0.0234(4) 0.0656(11) Uani 1 1 d . . . . .
H15 H 0.2867 0.3298 -0.0416 0.079 Uiso 1 1 calc R U . . .
F6 F 0.9358(5) 0.3635(6) 0.2580(4) 0.140(2) Uani 1 1 d . . . . .
C11 C 0.7609(5) 0.3617(5) 0.0662(3) 0.0602(11) Uani 1 1 d . . . . .
H11 H 0.8516 0.3568 0.0141 0.072 Uiso 1 1 calc R U . . .
C24 C 0.1932(5) 0.1802(5) 0.3531(4) 0.0678(12) Uani 1 1 d . . . . .
H24 H 0.1773 0.2492 0.3968 0.081 Uiso 1 1 calc R U . . .
C10 C 0.7637(5) 0.3846(4) 0.1626(4) 0.0573(10) Uani 1 1 d . . . . .
C18 C 0.6264(5) 0.0510(4) 0.1632(4) 0.0610(11) Uani 1 1 d . . . . .
C8 C 0.5726(7) 0.1606(6) 0.4515(4) 0.0799(15) Uani 1 1 d . . . . .
H8 H 0.6293 0.1055 0.3988 0.096 Uiso 1 1 calc R U . . .
C17 C 0.7773(7) -0.0115(6) 0.1007(5) 0.0851(17) Uani 1 1 d . . . . .
F9 F 0.8418(8) -0.0856(9) 0.1552(6) 0.217(4) Uani 1 1 d . . . . .
C14 C 0.5075(6) 0.3527(5) -0.0980(4) 0.0679(12) Uani 1 1 d . . . . .
H14 H 0.5105 0.3627 -0.1674 0.082 Uiso 1 1 calc R U . . .
C7 C 0.5815(9) 0.1346(7) 0.5503(5) 0.0915(18) Uani 1 1 d . . . . .
H7 H 0.6430 0.0637 0.5637 0.110 Uiso 1 1 calc R U . . .
C21 C 0.2362(7) -0.0189(6) 0.2265(5) 0.0786(15) Uani 1 1 d . . . . .
H21 H 0.2521 -0.0861 0.1811 0.094 Uiso 1 1 calc R U . . .
C3 C 0.3089(6) 0.4515(5) 0.4841(4) 0.0699(13) Uani 1 1 d . . . . .
H3 H 0.2629 0.5060 0.5395 0.084 Uiso 1 1 calc R U . . .
F8 F 0.8675(6) 0.0677(5) 0.0592(7) 0.208(4) Uani 1 1 d . . . . .
C9 C 0.9041(6) 0.4194(7) 0.1786(5) 0.0824(16) Uani 1 1 d . . . . .
C6 C 0.4991(9) 0.2142(8) 0.6283(5) 0.096(2) Uani 1 1 d . . . . .
H6 H 0.5007 0.1972 0.6963 0.116 Uiso 1 1 calc R U . . .
C23 C 0.0783(6) 0.1100(6) 0.3630(6) 0.0868(18) Uani 1 1 d . . . . .
H23 H -0.0129 0.1296 0.4134 0.104 Uiso 1 1 calc R U . . .
C22 C 0.1005(7) 0.0095(6) 0.2968(6) 0.0866(17) Uani 1 1 d . . . . .
H22 H 0.0232 -0.0382 0.3003 0.104 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V001 O1 1.928(3) . ?
V001 O2 1.934(3) . ?
V001 O3 1.944(3) . ?
V001 N2 2.132(4) . ?
V001 N1 2.148(4) . ?
V001 N3 2.181(4) . ?
O1 C2 1.314(5) . ?
O2 C10 1.300(5) . ?
F1 C1 1.339(6) . ?
O3 C18 1.298(6) . ?
N3 C20 1.342(6) . ?
N3 C24 1.344(6) . ?
F3 C1 1.307(6) . ?
N2 C16 1.341(6) . ?
N2 C12 1.352(5) . ?
F2 C1 1.325(7) . ?
C16 C15 1.381(7) . ?
C16 H16 0.9300 . ?
C1 C2 1.495(7) . ?
C19 C18 1.349(7) . ?
C19 C20 1.435(7) . ?
C19 H19 0.9300 . ?
N1 C4 1.349(6) . ?
N1 C8 1.350(7) . ?
F7 C17 1.304(8) . ?
C12 C13 1.393(6) . ?
C12 C11 1.450(6) . ?
C5 C6 1.376(10) . ?
C5 C4 1.384(8) . ?
C5 H5 0.9300 . ?
C20 C21 1.405(7) . ?
C13 C14 1.359(8) . ?
C13 H13 0.9300 . ?
F5 C9 1.299(7) . ?
F4 C9 1.328(9) . ?
C2 C3 1.331(7) . ?
C4 C3 1.451(8) . ?
C15 C14 1.393(7) . ?
C15 H15 0.9300 . ?
F6 C9 1.291(8) . ?
C11 C10 1.340(7) . ?
C11 H11 0.9300 . ?
C24 C23 1.367(7) . ?
C24 H24 0.9300 . ?
C10 C9 1.492(7) . ?
C18 C17 1.504(7) . ?
C8 C7 1.371(8) . ?
C8 H8 0.9300 . ?
C17 F9 1.268(9) . ?
C17 F8 1.272(8) . ?
C14 H14 0.9300 . ?
C7 C6 1.360(11) . ?
C7 H7 0.9300 . ?
C21 C22 1.354(9) . ?
C21 H21 0.9300 . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C23 C22 1.378(10) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V001 O2 97.07(14) . . ?
O1 V001 O3 172.83(13) . . ?
O2 V001 O3 90.04(14) . . ?
O1 V001 N2 89.15(13) . . ?
O2 V001 N2 88.74(13) . . ?
O3 V001 N2 90.12(14) . . ?
O1 V001 N1 89.42(15) . . ?
O2 V001 N1 88.62(14) . . ?
O3 V001 N1 91.64(15) . . ?
N2 V001 N1 176.83(13) . . ?
O1 V001 N3 89.75(14) . . ?
O2 V001 N3 173.18(14) . . ?
O3 V001 N3 83.14(14) . . ?
N2 V001 N3 91.56(13) . . ?
N1 V001 N3 91.27(14) . . ?
C2 O1 V001 127.7(3) . . ?
C10 O2 V001 122.0(3) . . ?
C18 O3 V001 123.7(3) . . ?
C20 N3 C24 118.6(4) . . ?
C20 N3 V001 122.9(3) . . ?
C24 N3 V001 118.4(3) . . ?
C16 N2 C12 118.9(4) . . ?
C16 N2 V001 119.2(3) . . ?
C12 N2 V001 121.8(3) . . ?
N2 C16 C15 123.2(4) . . ?
N2 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
F3 C1 F2 106.8(5) . . ?
F3 C1 F1 105.5(5) . . ?
F2 C1 F1 105.6(5) . . ?
F3 C1 C2 114.5(5) . . ?
F2 C1 C2 112.0(5) . . ?
F1 C1 C2 111.8(4) . . ?
C18 C19 C20 123.7(5) . . ?
C18 C19 H19 118.1 . . ?
C20 C19 H19 118.1 . . ?
C4 N1 C8 117.2(5) . . ?
C4 N1 V001 125.2(4) . . ?
C8 N1 V001 117.5(4) . . ?
N2 C12 C13 120.1(4) . . ?
N2 C12 C11 120.7(4) . . ?
C13 C12 C11 119.0(4) . . ?
C6 C5 C4 119.9(6) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N3 C20 C21 120.1(4) . . ?
N3 C20 C19 120.8(4) . . ?
C21 C20 C19 119.1(5) . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O1 C2 C3 128.4(4) . . ?
O1 C2 C1 111.4(4) . . ?
C3 C2 C1 120.2(5) . . ?
N1 C4 C5 121.4(5) . . ?
N1 C4 C3 120.5(4) . . ?
C5 C4 C3 118.1(5) . . ?
C16 C15 C14 117.7(5) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C10 C11 C12 125.7(4) . . ?
C10 C11 H11 117.1 . . ?
C12 C11 H11 117.1 . . ?
N3 C24 C23 123.1(5) . . ?
N3 C24 H24 118.4 . . ?
C23 C24 H24 118.4 . . ?
O2 C10 C11 128.3(4) . . ?
O2 C10 C9 112.5(4) . . ?
C11 C10 C9 119.1(4) . . ?
O3 C18 C19 126.6(4) . . ?
O3 C18 C17 113.0(5) . . ?
C19 C18 C17 120.3(5) . . ?
N1 C8 C7 123.5(6) . . ?
N1 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
F9 C17 F8 106.4(8) . . ?
F9 C17 F7 103.1(7) . . ?
F8 C17 F7 106.2(7) . . ?
F9 C17 C18 112.2(6) . . ?
F8 C17 C18 112.9(5) . . ?
F7 C17 C18 115.2(6) . . ?
C13 C14 C15 119.2(5) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C6 C7 C8 118.9(6) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C22 C21 C20 120.3(6) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C2 C3 C4 127.4(5) . . ?
C2 C3 H3 116.3 . . ?
C4 C3 H3 116.3 . . ?
F6 C9 F5 109.2(6) . . ?
F6 C9 F4 104.5(7) . . ?
F5 C9 F4 102.7(6) . . ?
F6 C9 C10 113.0(5) . . ?
F5 C9 C10 115.2(6) . . ?
F4 C9 C10 111.2(5) . . ?
C7 C6 C5 118.9(6) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C24 C23 C22 118.6(5) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C21 C22 C23 119.2(5) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N2 C16 C15 1.1(7) . . . . ?
V001 N2 C16 C15 -176.6(4) . . . . ?
C16 N2 C12 C13 -2.3(6) . . . . ?
V001 N2 C12 C13 175.3(3) . . . . ?
C16 N2 C12 C11 173.7(4) . . . . ?
V001 N2 C12 C11 -8.7(5) . . . . ?
C24 N3 C20 C21 4.4(7) . . . . ?
V001 N3 C20 C21 -171.1(4) . . . . ?
C24 N3 C20 C19 -173.3(5) . . . . ?
V001 N3 C20 C19 11.2(6) . . . . ?
C18 C19 C20 N3 16.9(8) . . . . ?
C18 C19 C20 C21 -160.8(5) . . . . ?
N2 C12 C13 C14 2.2(7) . . . . ?
C11 C12 C13 C14 -173.9(5) . . . . ?
V001 O1 C2 C3 -10.6(7) . . . . ?
V001 O1 C2 C1 172.0(3) . . . . ?
F3 C1 C2 O1 -179.0(4) . . . . ?
F2 C1 C2 O1 59.3(6) . . . . ?
F1 C1 C2 O1 -59.1(6) . . . . ?
F3 C1 C2 C3 3.4(7) . . . . ?
F2 C1 C2 C3 -118.3(6) . . . . ?
F1 C1 C2 C3 123.3(5) . . . . ?
C8 N1 C4 C5 0.3(8) . . . . ?
V001 N1 C4 C5 -177.7(4) . . . . ?
C8 N1 C4 C3 -179.2(5) . . . . ?
V001 N1 C4 C3 2.8(6) . . . . ?
C6 C5 C4 N1 -2.2(9) . . . . ?
C6 C5 C4 C3 177.3(6) . . . . ?
N2 C16 C15 C14 0.2(7) . . . . ?
N2 C12 C11 C10 -14.4(7) . . . . ?
C13 C12 C11 C10 161.6(5) . . . . ?
C20 N3 C24 C23 -1.8(8) . . . . ?
V001 N3 C24 C23 173.8(5) . . . . ?
V001 O2 C10 C11 28.7(7) . . . . ?
V001 O2 C10 C9 -154.8(4) . . . . ?
C12 C11 C10 O2 5.0(8) . . . . ?
C12 C11 C10 C9 -171.2(5) . . . . ?
V001 O3 C18 C19 -36.0(6) . . . . ?
V001 O3 C18 C17 147.9(4) . . . . ?
C20 C19 C18 O3 -6.3(8) . . . . ?
C20 C19 C18 C17 169.6(5) . . . . ?
C4 N1 C8 C7 0.7(9) . . . . ?
V001 N1 C8 C7 178.9(5) . . . . ?
O3 C18 C17 F9 71.1(8) . . . . ?
C19 C18 C17 F9 -105.4(8) . . . . ?
O3 C18 C17 F8 -49.1(9) . . . . ?
C19 C18 C17 F8 134.5(8) . . . . ?
O3 C18 C17 F7 -171.3(6) . . . . ?
C19 C18 C17 F7 12.2(9) . . . . ?
C12 C13 C14 C15 -0.9(8) . . . . ?
C16 C15 C14 C13 -0.3(7) . . . . ?
N1 C8 C7 C6 0.2(11) . . . . ?
N3 C20 C21 C22 -3.8(9) . . . . ?
C19 C20 C21 C22 173.9(6) . . . . ?
O1 C2 C3 C4 -1.3(8) . . . . ?
C1 C2 C3 C4 175.9(5) . . . . ?
N1 C4 C3 C2 4.8(8) . . . . ?
C5 C4 C3 C2 -174.7(5) . . . . ?
O2 C10 C9 F6 45.6(8) . . . . ?
C11 C10 C9 F6 -137.6(6) . . . . ?
O2 C10 C9 F5 172.1(6) . . . . ?
C11 C10 C9 F5 -11.1(9) . . . . ?
O2 C10 C9 F4 -71.6(7) . . . . ?
C11 C10 C9 F4 105.2(6) . . . . ?
C8 C7 C6 C5 -2.0(11) . . . . ?
C4 C5 C6 C7 3.0(11) . . . . ?
N3 C24 C23 C22 -1.5(10) . . . . ?
C20 C21 C22 C23 0.5(11) . . . . ?
C24 C23 C22 C21 2.0(11) . . . . ?

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.156

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_audit_block_doi                 10.5517/ccdc.csd.cc1zbrdg
_database_code_depnum_ccdc_archive 'CCDC 1827586'
_audit_update_record             
;
2018-03-05 deposited with the CCDC.
2018-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H12 F9 N6 O3 V'
_chemical_formula_sum            'C21 H12 F9 N6 O3 V'
_chemical_formula_weight         618.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5584(18)
_cell_length_b                   10.2431(19)
_cell_length_c                   14.555(3)
_cell_angle_alpha                73.757(15)
_cell_angle_beta                 88.851(15)
_cell_angle_gamma                66.864(14)
_cell_volume                     1251.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2000
_cell_measurement_theta_min      1.465
_cell_measurement_theta_max      29.682

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.500
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'IPDS 2T (Stoe & Cie)'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24426
_diffrn_reflns_av_unetI/netI     0.1295
_diffrn_reflns_av_R_equivalents  0.1641
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.465
_diffrn_reflns_theta_max         29.682
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6980
_reflns_number_gt                2727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.026(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6980
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2513
_refine_ls_R_factor_gt           0.1362
_refine_ls_wR_factor_ref         0.4433
_refine_ls_wR_factor_gt          0.3886
_refine_ls_goodness_of_fit_ref   1.236
_refine_ls_restrained_S_all      1.236
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.79421(16) 0.44502(14) 0.76649(10) 0.0609(5) Uani 1 1 d . . . . .
O3 O 1.0061(7) 0.3088(6) 0.7940(4) 0.0733(16) Uani 1 1 d . . . . .
O2 O 0.7212(7) 0.3517(6) 0.8806(4) 0.0736(16) Uani 1 1 d . . . . .
C14 C 0.7213(13) 0.1520(12) 1.0076(7) 0.078(3) Uani 1 1 d . . . . .
O1 O 0.8495(6) 0.5508(6) 0.6466(4) 0.0674(14) Uani 1 1 d . . . . .
N4 N 1.1160(8) 0.4682(8) 0.8204(5) 0.0685(18) Uani 1 1 d . . . . .
N6 N 0.7313(9) 0.1333(8) 0.8497(6) 0.0747(19) Uani 1 1 d . . . . .
C9 C 0.9934(10) 0.5581(9) 0.8569(6) 0.064(2) Uani 1 1 d . . . . .
N3 N 0.8480(8) 0.5697(7) 0.8424(5) 0.0643(16) Uani 1 1 d . . . . .
N1 N 0.5753(8) 0.6217(7) 0.7140(5) 0.0642(17) Uani 1 1 d . . . . .
N5 N 0.7425(9) 0.3053(8) 0.7005(5) 0.0719(19) Uani 1 1 d . . . . .
N2 N 0.6737(8) 0.7941(8) 0.6169(6) 0.0731(19) Uani 1 1 d . . . . .
C18 C 0.6709(14) 0.1397(12) 0.6012(8) 0.098(3) Uani 1 1 d . . . . .
H18 H 0.6510 0.0798 0.5682 0.117 Uiso 1 1 calc R U . . .
C16 C 0.7211(11) 0.1834(9) 0.7492(7) 0.074(2) Uani 1 1 d . . . . .
F7 F 0.6330(15) 0.2512(11) 1.0490(7) 0.183(4) Uani 1 1 d . . . . .
F9 F 0.6682(13) 0.0503(10) 1.0263(5) 0.164(4) Uani 1 1 d . . . . .
C15 C 0.7257(9) 0.2201(9) 0.8991(6) 0.064(2) Uani 1 1 d . . . . .
C6 C 0.3041(11) 0.7113(12) 0.7271(7) 0.082(3) Uani 1 1 d . . . . .
H6 H 0.2195 0.6908 0.7513 0.098 Uiso 1 1 calc R U . . .
C3 C 0.5526(10) 0.7598(9) 0.6616(6) 0.064(2) Uani 1 1 d . . . . .
C10 C 1.0263(11) 0.6432(9) 0.9072(6) 0.070(2) Uani 1 1 d . . . . .
H10 H 1.1277 0.6360 0.9157 0.084 Uiso 1 1 calc R U . . .
C12 C 0.7616(12) 0.7451(10) 0.9330(7) 0.079(2) Uani 1 1 d . . . . .
H12 H 0.6798 0.8077 0.9594 0.095 Uiso 1 1 calc R U . . .
C7 C 0.4466(11) 0.6013(11) 0.7448(6) 0.073(2) Uani 1 1 d . . . . .
H7 H 0.4582 0.5040 0.7808 0.088 Uiso 1 1 calc R U . . .
F6 F 1.2666(10) 0.1528(11) 0.7469(10) 0.201(5) Uani 1 1 d . . . . .
C19 C 0.6812(14) 0.2675(13) 0.5530(7) 0.100(4) Uani 1 1 d . . . . .
H19 H 0.6615 0.3028 0.4849 0.120 Uiso 1 1 calc R U . . .
C025 C 1.2596(12) 0.2708(11) 0.7606(9) 0.087(3) Uani 1 1 d . . . . .
C11 C 0.9073(13) 0.7383(11) 0.9444(8) 0.087(3) Uani 1 1 d . . . . .
H11 H 0.9264 0.7984 0.9776 0.105 Uiso 1 1 calc R U . . .
C2 C 0.8022(10) 0.6924(10) 0.6123(6) 0.069(2) Uani 1 1 d . . . . .
C1 C 0.9146(14) 0.7421(13) 0.5608(9) 0.093(3) Uani 1 1 d . . . . .
C8 C 1.1123(10) 0.3598(9) 0.7956(6) 0.069(2) Uani 1 1 d . . . . .
C13 C 0.7368(11) 0.6593(9) 0.8826(6) 0.069(2) Uani 1 1 d . . . . .
H13 H 0.6364 0.6634 0.8758 0.083 Uiso 1 1 calc R U . . .
F3B F 1.051(3) 0.678(4) 0.596(2) 0.21(2) Uani 0.5 1 d . . P A 1
C20 C 0.7206(13) 0.3483(11) 0.6024(7) 0.088(3) Uani 1 1 d . . . . .
H20 H 0.7326 0.4358 0.5669 0.105 Uiso 1 1 calc R U . . .
F4 F 1.3041(13) 0.3436(10) 0.6932(8) 0.214(6) Uani 1 1 d . . . . .
C17 C 0.6905(13) 0.0971(11) 0.7026(8) 0.093(3) Uani 1 1 d . . . . .
H17 H 0.6823 0.0079 0.7388 0.112 Uiso 1 1 calc R U . . .
F5 F 1.3754(10) 0.2166(15) 0.8308(9) 0.207(6) Uani 1 1 d . . . . .
C4 C 0.4096(10) 0.8786(11) 0.6401(8) 0.082(3) Uani 1 1 d . . . . .
H4 H 0.3999 0.9748 0.6032 0.098 Uiso 1 1 calc R U . . .
F2B F 0.881(3) 0.879(2) 0.526(3) 0.155(15) Uani 0.5 1 d . . P A 2
C5 C 0.2824(12) 0.8552(12) 0.6729(8) 0.090(3) Uani 1 1 d . . . . .
H5 H 0.1836 0.9341 0.6590 0.108 Uiso 1 1 calc R U . . .
F1B F 0.906(4) 0.721(4) 0.4700(17) 0.162(9) Uani 0.5 1 d . . P A .
F8 F 0.8459(13) 0.1035(15) 1.0546(6) 0.202(5) Uani 1 1 d . . . . .
F2A F 0.853(5) 0.850(6) 0.481(3) 0.22(2) Uani 0.5 1 d . . P A .
F10 F 1.033(3) 0.641(2) 0.553(3) 0.168(15) Uani 0.5 1 d . . P A .
F11 F 0.953(3) 0.824(4) 0.607(3) 0.168(10) Uani 0.5 1 d . . P A .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O3 1.925(6) . ?
V1 O2 1.936(6) . ?
V1 O1 1.963(6) . ?
V1 N3 2.109(7) . ?
V1 N1 2.133(7) . ?
V1 N5 2.135(6) . ?
O3 C8 1.315(10) . ?
O2 C15 1.282(9) . ?
C14 F8 1.229(13) . ?
C14 F9 1.291(11) . ?
C14 F7 1.325(13) . ?
C14 C15 1.545(12) . ?
O1 C2 1.283(10) . ?
N4 C8 1.272(10) . ?
N4 C9 1.380(10) . ?
N6 C15 1.276(10) . ?
N6 C16 1.400(11) . ?
C9 N3 1.364(10) . ?
C9 C10 1.406(11) . ?
N3 C13 1.350(10) . ?
N1 C3 1.338(10) . ?
N1 C7 1.374(10) . ?
N5 C16 1.343(10) . ?
N5 C20 1.366(11) . ?
N2 C2 1.277(11) . ?
N2 C3 1.431(10) . ?
C18 C19 1.342(14) . ?
C18 C17 1.411(15) . ?
C18 H18 0.9500 . ?
C16 C17 1.369(12) . ?
C6 C7 1.355(13) . ?
C6 C5 1.398(14) . ?
C6 H6 0.9500 . ?
C3 C4 1.394(12) . ?
C10 C11 1.391(13) . ?
C10 H10 0.9500 . ?
C12 C11 1.378(15) . ?
C12 C13 1.377(11) . ?
C12 H12 0.9500 . ?
C7 H7 0.9500 . ?
F6 C025 1.255(12) . ?
C19 C20 1.390(12) . ?
C19 H19 0.9500 . ?
C025 F4 1.234(13) . ?
C025 F5 1.350(14) . ?
C025 C8 1.516(13) . ?
C11 H11 0.9500 . ?
C2 C1 1.470(13) . ?
C1 F10 1.231(19) . ?
C1 F3B 1.25(2) . ?
C1 F2B 1.26(2) . ?
C1 F2A 1.31(4) . ?
C1 F11 1.35(2) . ?
C1 F1B 1.40(2) . ?
C13 H13 0.9500 . ?
F3B F10 0.87(4) . ?
F3B F11 1.46(4) . ?
C20 H20 0.9500 . ?
C17 H17 0.9500 . ?
C4 C5 1.380(13) . ?
C4 H4 0.9500 . ?
F2B F2A 0.88(5) . ?
F2B F11 1.23(4) . ?
C5 H5 0.9500 . ?
F1B F2A 1.27(5) . ?
F1B F10 1.53(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 V1 O2 97.5(3) . . ?
O3 V1 O1 87.5(2) . . ?
O2 V1 O1 175.0(3) . . ?
O3 V1 N3 87.2(3) . . ?
O2 V1 N3 89.8(2) . . ?
O1 V1 N3 91.2(2) . . ?
O3 V1 N1 168.7(2) . . ?
O2 V1 N1 93.7(3) . . ?
O1 V1 N1 81.4(2) . . ?
N3 V1 N1 90.8(3) . . ?
O3 V1 N5 91.2(3) . . ?
O2 V1 N5 86.0(2) . . ?
O1 V1 N5 93.1(2) . . ?
N3 V1 N5 175.4(3) . . ?
N1 V1 N5 91.6(3) . . ?
C8 O3 V1 119.7(5) . . ?
C15 O2 V1 123.2(5) . . ?
F8 C14 F9 109.4(11) . . ?
F8 C14 F7 102.2(11) . . ?
F9 C14 F7 104.6(10) . . ?
F8 C14 C15 113.0(9) . . ?
F9 C14 C15 113.8(8) . . ?
F7 C14 C15 112.9(9) . . ?
C2 O1 V1 125.6(5) . . ?
C8 N4 C9 121.7(7) . . ?
C15 N6 C16 120.1(7) . . ?
N3 C9 N4 122.9(7) . . ?
N3 C9 C10 121.4(8) . . ?
N4 C9 C10 115.7(7) . . ?
C13 N3 C9 118.1(7) . . ?
C13 N3 V1 119.4(6) . . ?
C9 N3 V1 122.4(5) . . ?
C3 N1 C7 115.7(8) . . ?
C3 N1 V1 124.7(5) . . ?
C7 N1 V1 119.0(6) . . ?
C16 N5 C20 118.1(7) . . ?
C16 N5 V1 124.2(6) . . ?
C20 N5 V1 117.6(5) . . ?
C2 N2 C3 121.7(7) . . ?
C19 C18 C17 117.8(9) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
N5 C16 C17 121.4(9) . . ?
N5 C16 N6 123.4(8) . . ?
C17 C16 N6 115.2(8) . . ?
N6 C15 O2 135.5(8) . . ?
N6 C15 C14 112.9(7) . . ?
O2 C15 C14 111.6(8) . . ?
C7 C6 C5 119.5(9) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N1 C3 C4 123.6(8) . . ?
N1 C3 N2 121.7(8) . . ?
C4 C3 N2 114.5(8) . . ?
C11 C10 C9 118.6(8) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C11 C12 C13 118.8(9) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C6 C7 N1 124.1(9) . . ?
C6 C7 H7 118.0 . . ?
N1 C7 H7 118.0 . . ?
C18 C19 C20 120.2(10) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
F4 C025 F6 111.8(12) . . ?
F4 C025 F5 102.5(11) . . ?
F6 C025 F5 100.8(10) . . ?
F4 C025 C8 115.0(9) . . ?
F6 C025 C8 115.6(9) . . ?
F5 C025 C8 109.3(10) . . ?
C12 C11 C10 119.7(8) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N2 C2 O1 129.5(8) . . ?
N2 C2 C1 116.4(9) . . ?
O1 C2 C1 114.1(9) . . ?
F10 C1 F3B 41(2) . . ?
F10 C1 F2B 126.2(16) . . ?
F10 C1 F2A 115(3) . . ?
F3B C1 F2A 129.4(18) . . ?
F2B C1 F2A 40(2) . . ?
F10 C1 F11 107.8(19) . . ?
F3B C1 F11 68(2) . . ?
F2B C1 F11 56.2(18) . . ?
F2A C1 F11 96(2) . . ?
F10 C1 F1B 70(2) . . ?
F3B C1 F1B 109(2) . . ?
F2B C1 F1B 93(2) . . ?
F2A C1 F1B 55(2) . . ?
F11 C1 F1B 142(2) . . ?
F10 C1 C2 114.4(12) . . ?
F3B C1 C2 118.1(12) . . ?
F2B C1 C2 119.3(14) . . ?
F2A C1 C2 112.5(16) . . ?
F11 C1 C2 109.8(15) . . ?
F1B C1 C2 104.5(14) . . ?
N4 C8 O3 133.1(8) . . ?
N4 C8 C025 114.0(8) . . ?
O3 C8 C025 112.9(8) . . ?
N3 C13 C12 123.3(8) . . ?
N3 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
F10 F3B C1 68.3(17) . . ?
F10 F3B F11 125(3) . . ?
C1 F3B F11 59.3(15) . . ?
N5 C20 C19 121.8(9) . . ?
N5 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C16 C17 C18 120.4(9) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C5 C4 C3 119.5(10) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
F2A F2B F11 138(4) . . ?
F2A F2B C1 73(4) . . ?
F11 F2B C1 65.7(15) . . ?
C4 C5 C6 117.6(10) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
F2A F1B C1 58.7(19) . . ?
F2A F1B F10 100(3) . . ?
C1 F1B F10 49.5(11) . . ?
F2B F2A F1B 128(6) . . ?
F2B F2A C1 67(3) . . ?
F1B F2A C1 66(3) . . ?
F3B F10 C1 70(2) . . ?
F3B F10 F1B 126(3) . . ?
C1 F10 F1B 60.1(15) . . ?
F2B F11 C1 58.1(17) . . ?
C1 F11 F3B 52.4(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N4 C9 N3 -20.8(13) . . . . ?
C8 N4 C9 C10 161.8(8) . . . . ?
N4 C9 N3 C13 179.0(7) . . . . ?
C10 C9 N3 C13 -3.7(12) . . . . ?
N4 C9 N3 V1 2.3(11) . . . . ?
C10 C9 N3 V1 179.6(6) . . . . ?
C20 N5 C16 C17 5.3(14) . . . . ?
V1 N5 C16 C17 -179.0(7) . . . . ?
C20 N5 C16 N6 -176.1(9) . . . . ?
V1 N5 C16 N6 -0.4(13) . . . . ?
C15 N6 C16 N5 16.7(14) . . . . ?
C15 N6 C16 C17 -164.6(9) . . . . ?
C16 N6 C15 O2 -5.2(16) . . . . ?
C16 N6 C15 C14 173.9(8) . . . . ?
V1 O2 C15 N6 -23.1(14) . . . . ?
V1 O2 C15 C14 157.7(6) . . . . ?
F8 C14 C15 N6 101.3(12) . . . . ?
F9 C14 C15 N6 -24.3(13) . . . . ?
F7 C14 C15 N6 -143.3(10) . . . . ?
F8 C14 C15 O2 -79.3(13) . . . . ?
F9 C14 C15 O2 155.1(10) . . . . ?
F7 C14 C15 O2 36.0(13) . . . . ?
C7 N1 C3 C4 1.3(12) . . . . ?
V1 N1 C3 C4 -170.2(7) . . . . ?
C7 N1 C3 N2 -173.8(7) . . . . ?
V1 N1 C3 N2 14.6(11) . . . . ?
C2 N2 C3 N1 10.9(13) . . . . ?
C2 N2 C3 C4 -164.6(8) . . . . ?
N3 C9 C10 C11 1.4(13) . . . . ?
N4 C9 C10 C11 178.9(8) . . . . ?
C5 C6 C7 N1 1.2(14) . . . . ?
C3 N1 C7 C6 -1.6(12) . . . . ?
V1 N1 C7 C6 170.5(7) . . . . ?
C17 C18 C19 C20 4.4(19) . . . . ?
C13 C12 C11 C10 -1.5(15) . . . . ?
C9 C10 C11 C12 1.2(14) . . . . ?
C3 N2 C2 O1 -3.0(15) . . . . ?
C3 N2 C2 C1 177.4(9) . . . . ?
V1 O1 C2 N2 -33.3(13) . . . . ?
V1 O1 C2 C1 146.4(8) . . . . ?
N2 C2 C1 F10 -176(3) . . . . ?
O1 C2 C1 F10 4(3) . . . . ?
N2 C2 C1 F3B 138(3) . . . . ?
O1 C2 C1 F3B -42(3) . . . . ?
N2 C2 C1 F2B 1(3) . . . . ?
O1 C2 C1 F2B -179(3) . . . . ?
N2 C2 C1 F2A -43(3) . . . . ?
O1 C2 C1 F2A 137(3) . . . . ?
N2 C2 C1 F11 63(2) . . . . ?
O1 C2 C1 F11 -117(2) . . . . ?
N2 C2 C1 F1B -101(2) . . . . ?
O1 C2 C1 F1B 79(2) . . . . ?
C9 N4 C8 O3 2.2(15) . . . . ?
C9 N4 C8 C025 -178.0(8) . . . . ?
V1 O3 C8 N4 33.4(13) . . . . ?
V1 O3 C8 C025 -146.5(7) . . . . ?
F4 C025 C8 N4 -55.8(15) . . . . ?
F6 C025 C8 N4 171.5(11) . . . . ?
F5 C025 C8 N4 58.7(13) . . . . ?
F4 C025 C8 O3 124.1(12) . . . . ?
F6 C025 C8 O3 -8.6(15) . . . . ?
F5 C025 C8 O3 -121.4(11) . . . . ?
C9 N3 C13 C12 3.5(12) . . . . ?
V1 N3 C13 C12 -179.7(7) . . . . ?
C11 C12 C13 N3 -0.9(14) . . . . ?
F2A C1 F3B F10 -83(4) . . . . ?
F11 C1 F3B F10 -163(3) . . . . ?
F1B C1 F3B F10 -23(3) . . . . ?
C2 C1 F3B F10 96(2) . . . . ?
F10 C1 F3B F11 163(3) . . . . ?
F2A C1 F3B F11 80(4) . . . . ?
F1B C1 F3B F11 140(2) . . . . ?
C2 C1 F3B F11 -101.5(19) . . . . ?
C16 N5 C20 C19 -1.7(15) . . . . ?
V1 N5 C20 C19 -177.7(9) . . . . ?
C18 C19 C20 N5 -3.2(18) . . . . ?
N5 C16 C17 C18 -4.1(16) . . . . ?
N6 C16 C17 C18 177.2(10) . . . . ?
C19 C18 C17 C16 -0.9(18) . . . . ?
N1 C3 C4 C5 -0.7(14) . . . . ?
N2 C3 C4 C5 174.7(9) . . . . ?
F10 C1 F2B F2A 86(4) . . . . ?
F11 C1 F2B F2A 174(4) . . . . ?
F1B C1 F2B F2A 18(4) . . . . ?
C2 C1 F2B F2A -91(4) . . . . ?
F10 C1 F2B F11 -88(3) . . . . ?
F2A C1 F2B F11 -174(4) . . . . ?
F1B C1 F2B F11 -156.1(18) . . . . ?
C2 C1 F2B F11 95(2) . . . . ?
C3 C4 C5 C6 0.2(15) . . . . ?
C7 C6 C5 C4 -0.5(15) . . . . ?
F10 C1 F1B F2A -141(2) . . . . ?
F3B C1 F1B F2A -126(2) . . . . ?
F2B C1 F1B F2A -14(2) . . . . ?
F11 C1 F1B F2A -47(4) . . . . ?
C2 C1 F1B F2A 108(2) . . . . ?
F3B C1 F1B F10 15.8(18) . . . . ?
F2B C1 F1B F10 127.4(17) . . . . ?
F2A C1 F1B F10 141(2) . . . . ?
F11 C1 F1B F10 94(3) . . . . ?
C2 C1 F1B F10 -111.2(13) . . . . ?
F11 F2B F2A F1B -17(9) . . . . ?
C1 F2B F2A F1B -26(4) . . . . ?
F11 F2B F2A C1 8(5) . . . . ?
C1 F1B F2A F2B 26(4) . . . . ?
F10 F1B F2A F2B -3(6) . . . . ?
F10 F1B F2A C1 -28.8(16) . . . . ?
F10 C1 F2A F2B -118(3) . . . . ?
F11 C1 F2A F2B -5(3) . . . . ?
F1B C1 F2A F2B -158(4) . . . . ?
C2 C1 F2A F2B 109(3) . . . . ?
F10 C1 F2A F1B 40(2) . . . . ?
F3B C1 F2A F1B 86(4) . . . . ?
F2B C1 F2A F1B 158(4) . . . . ?
F11 C1 F2A F1B 153(2) . . . . ?
C2 C1 F2A F1B -93(3) . . . . ?
F11 F3B F10 C1 -18(3) . . . . ?
C1 F3B F10 F1B 25(2) . . . . ?
F11 F3B F10 F1B 6(5) . . . . ?
F2A C1 F10 F3B 123(3) . . . . ?
F11 C1 F10 F3B 17(3) . . . . ?
F1B C1 F10 F3B 157(3) . . . . ?
C2 C1 F10 F3B -105(2) . . . . ?
F3B C1 F10 F1B -157(3) . . . . ?
F2B C1 F10 F1B -79(3) . . . . ?
F2A C1 F10 F1B -34.4(19) . . . . ?
F11 C1 F10 F1B -140(2) . . . . ?
C2 C1 F10 F1B 97.6(17) . . . . ?
F2A F1B F10 F3B 6(4) . . . . ?
C1 F1B F10 F3B -27(3) . . . . ?
F2A F1B F10 C1 32.8(19) . . . . ?
F2A F2B F11 C1 -9(5) . . . . ?
F10 C1 F11 F2B 122(2) . . . . ?
F2A C1 F11 F2B 4(3) . . . . ?
F1B C1 F11 F2B 41(3) . . . . ?
C2 C1 F11 F2B -112.7(18) . . . . ?
F10 C1 F11 F3B -12(2) . . . . ?
F2A C1 F11 F3B -130(2) . . . . ?
F1B C1 F11 F3B -93(3) . . . . ?
C2 C1 F11 F3B 113.3(14) . . . . ?
F10 F3B F11 C1 20(3) . . . . ?

_refine_diff_density_max         0.751
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.135


_exptl_crystal_recrystallization_method Sublimation
